1-Phenethylamine, (+)- → HCID 178462038, compound

HRID 1781577Notes

Reaction equation

HRID 1781577 reaction equation
[C:1]([N:3]=[C:4](OC1C=CC=CC=1)[NH:5][C:6]1[CH:7]=[N:8][CH:9]=[N:10][CH:11]=1)#[N:2].[CH3:19][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[C:1]([N:3]=[C:4]([NH:27][C@@H:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:19])[NH:5][C:6]1[CH:11]=[N:10][CH:9]=[N:8][CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 178512303HCID 178512303, compound

Product 1

HCID 178462038HCID 178462038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of N'-cyano-N-(5-pyrimidyl)-O-phenylisourea (0.5 g, 0.00209 mol), (R)-α-methylbenzylamine (1.0 mL) and DMF (4 mL) was kept, under nitrogen, at ambient temperature for 18 hours and concentrated in vacuo. The residue was allowed to crystallize from EtOAc-tert-butyl methyl ether. The solid was triturated with Et2O and tert-butyl methyl ether and crystallized from EtOAc to give product: NMR (CDCl3) δ1.61 (d, 3H), 4.92 (m, 1H), 6.05 (broad s, 1H), 7.38 (m, 6H), 8.56 (s, 2H), 8.97 (s, 1H); IR (Nujol) 3262, 3109, 3054, 2174, 1600, 1570 cm-1 ; MS m/z (relative intensity) 266 (M+, 100), 251 (24.3), 161 (4.0), 146 (33.0), 120 (40.5), 105 (100).

Workup

  1. concentrationconcentrated in vacuo
  2. customto crystallize from EtOAc-tert-butyl methyl ether
  3. customThe solid was triturated with Et2O and tert-butyl methyl ether
  4. customcrystallized from EtOAc
  5. customto give product

Sources & evidence

ORD record
ord-e078ab19abb14e4ab8ca11ba7e1f1bc5
Source dataset
uspto-grants-1997_05
Patent number
US05633374

Reaction notes

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